Who did Crystal Harris Hefner date after Hugh Hefner? Since the Playboy founder’s death, she’s been linked to a SpaceX engineer and a 23-year-old tennis pro – so who’s giving her a ‘beautiful relationship’?

May 31 , 2024

Crystal Harris Hefner poses with her former husband, the late Playboy founder Hugh Hefner, at the Playboy Mansion, back in the day. Photo: @crystalhefner/Instagram

Crystal Harris shot to fame as the young Playboy Bunny who married notorious publisher Hugh Hefner, who was 60 years her senior – she got a multimillion-dollar payout after his 2017 death

Since then, Harris has been in more low-key relationships with men her age – or younger – that have involved birthday trips to Mexico, walks in Central Park, and meeting on celebrity dating app Raya

As the founder and editor-in-chief of Playboy magazine, Hugh Hefner was famous for his many girlfriends, wild parties and controversial lifestyle. Surprisingly though, despite all the women that passed through the Playboy mansion over the years, Hefner was only married three times: first to Mildred Williams between 1949 and 1959, then to Kimberley Conrad between 1989 and 2009, and finally to former Playboy model Crystal Harris, from 2012 until his passing in 2017, per Business Insider.

Crystal Harris Hefner alongside Playboy founder and former husband Hugh Hefner. Photo: @crystalhefner/Instagram

Hugh proposed to Crystal in 2010, when she was 23 and he was 83 – yes, they had a 60-year age gap. And while their marriage might appear to follow a typical gold-digger narrative at first glance, Crystal was actually never in Hugh’s will. In fact, the couple even signed an ironclad prenup, which meant she was unlikely to inherit any of his millions, per Us Weekly.

Crystal Harris poses for The New York Times in January. Photo: @crystalhefner/Instagram

Fortunately for Crystal, however, as they were still married when Hugh died, she was reportedly entitled to a substantial payout of US$7 million in cash as well as a US$5 million Hollywood Hills home that was left in a trust for her.

After processing Hugh’s death and her time in the Playboy Mansion, Crystal released a tell-all memoir, Only Say Good Things: Surviving Playboy and Finding Myself, this year, lifting the lid on their relationship. While she acknowledges she loved Hugh, she admits she was never “in love” with him.

Crystal Harris promotes her autobiography on Piers Morgan’s TV show in February. Photo: @crystalhefner/Instagram

“I realised I was dealing with a really big power imbalance,” she wrote in her book. “It seemed like a world of success and fantasy, but everyone’s having to sleep with an 80-year-old. There’s a price. Everything has a price.”

Now 38, Crystal has thrown herself back into the dating world, opting for men who are worlds away from her Playboy ex. Here are four beaux who she’s been linked to in recent years.

1. Nathan Levi, 36

Nathan Levi and Crystal Harris Hefner. Photo: Instagram